Research Question

Who was William Simson, the man named in the 1676 Kent County, Delaware land grant called Simpson’s Choice, and how does he connect to the later Simpson family of Mispillion Hundred?

This research examines whether William Simson of Kent County, Delaware, was a Scottish-Anglo border immigrant who entered Maryland as an indentured servant in the Blakiston household, later appeared in Delaware land records as the nominal patentee of Simpson’s Choice, and was probably the father of the William Simpson bound out in Kent County in 1699.

This page is a compact summary. Full citations and source analysis are provided in the complete PDF proof.

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Short Conclusion

The best-supported reconstruction is that William Simson was a man of Scottish-Anglo border origin who arrived in Maryland by 1668 as part of the household or labor network of John Blakiston. After completing a period of servitude, he likely remained in the Chesapeake-Delaware region as a land-poor tenant, tradesman, or laboring freeman.

In 1675-1676, he appears in land records associated with speculative grants at Raccoon Creek and in Kent County, Delaware. The Kent County tract, known as Simpson’s Choice, was granted in his name in 1676 but quickly passed into the hands of better-positioned land speculators. The pattern suggests that Simson served as a nominal or “straw” patentee: a man whose name was used to secure title before the land was transferred to the real financial actors behind the transaction.

By 1699, a 13-and-a-half-year-old boy named William Simpson was brought into Kent County court by John Walker and bound to serve until age twenty-one. No parent appeared in the record. Given the absence of any other plausible Simson/Simpson household in the county, the boy’s age, the local association with John Walker, and the lack of any surviving estate for the elder William, the bound-out boy was very likely the son of the earlier William Simson of Simpson’s Choice.

The documentary evidence does not produce a single record that states this relationship outright. Instead, the conclusion rests on the correlation of land records, court proceedings, negative evidence, local association, migration patterns, and Y-DNA evidence.

Why William Simson Matters

William Simson stands at the head of the known Simpson line in Kent County, Delaware. His record is fragmentary but unusually revealing.

He appears at the intersection of seventeenth-century indentured servitude, Maryland headright claims, Chesapeake-to-Delaware migration, speculative land acquisition under Governor Edmund Andros, the use of nominal patentees in early land transactions, the poverty and vulnerability of freed servants, and the later survival of a patrilineal Simpson family in Kent County.

His story helps explain how a man could appear briefly as the grantee of 400 acres and yet leave no estate, no continuing property record, and, apparently, a son bound out as an indigent child.

Key Evidence Used

  • 1676 Kent County land grant for Simpson’s Choice: establishes William Simson as patentee of the 400-acre tract.
  • 1678 Brinckloe-to-Edmondson assignment: connects Simpson’s Choice to the Edmondson/Richardson land-transfer network.
  • 1699 Kent County binding-out record for William Simpson: places a 13-and-a-half-year-old William Simpson in the same county and local network.
  • Maryland headright claim by John Blakiston: identifies a William Simson transported to Maryland in 1668.
  • St. Clement’s Manor records: place William Simson in the Blakiston Maryland context.
  • Big Y-DNA results for the Simpson lines: support a shared patrilineal Simpson origin and point toward the Scottish-Anglo border region.
  • Comparative analysis of alternate William Sim(p)sons: explains why other candidates are weaker.

The Land-Record Problem

The apparent contradiction begins with Simpson’s Choice.

On 25 March 1676, Governor Edmund Andros issued a 400-acre Kent County land warrant to William Simson. On its face, this looks like evidence that Simson was a substantial landholder. But the later record does not support that interpretation.

The tract quickly moved out of his control. By 1678, Justice John Brinckloe formally transferred Simpson’s Choice to John Edmondson, a Maryland-connected land speculator. Edmondson then conveyed the land to John Richardson, another prominent figure in early land acquisition. Simson himself does not appear as the public grantor in the recorded transfer.

This pattern is important. Under the Duke of York’s land laws, land generally had to be seated and improved before a patentee could freely transfer it. A poor freed servant would have struggled to clear and improve 400 acres. A well-connected magistrate or speculator, however, could help regularize title, satisfy formal requirements, and make the land marketable.

Together, the Raccoon Creek and Simpson’s Choice episodes suggest that William Simson was not functioning as a normal planter developing his own estate. He appears more plausibly as a nominal patentee whose name helped others obtain or perfect title.

The 1699 Binding-Out Record

The strongest local link between the elder William Simson and the later Kent County Simpson family is the 1699 court order involving a young servant boy named William Simpson.

In that record, John Walker brought the boy into court because he had come without an indenture. The court judged him to be about thirteen years and six months old and ordered him to serve Walker until age twenty-one. At the end of service, Walker was to provide the customary corn, clothes, and tools.

The boy’s age places his birth around 1685 or 1686, a plausible period for a son of the elder William Simson who had been active in the region during the 1670s. No parent appeared in court to bind him out. Walker was also not a random man: he had witnessed the 1678 assignment involving Simpson’s Choice, owned land near the relevant Kent County neighborhood, and took in other dependent children.

The 1699 record does not name the boy’s father. But in context, the most likely explanation is that this was the son of William Simson of Simpson’s Choice.

Negative Evidence

The argument also depends on what is missing.

Searches of Kent County deeds, probate material, tax lists, and early land records do not reveal another plausible William Simson or Simpson who could explain the 1699 boy. Nor do the records show the elder William developing another tract, acquiring later land, or leaving an estate.

That absence matters because the county was small and the name was uncommon in the surviving records. If another adult Simson/Simpson household had existed in the immediate area, it would be expected to appear somewhere in deeds, tax lists, probate, court records, or land transactions.

Y-DNA Evidence

Y-DNA evidence adds an independent line of support.

Big Y testing connects three Simpson lines to the same Y-DNA branch, R-FGC39762: a descendant of Moses Simpson through William, Davis Simpson descending through John and William, and a Simpson line documented in Eccles, Berwickshire.

The DNA supports the conclusion that the colonial Delaware Simpson lines share a common male Simpson ancestor. The connection to a documented Berwickshire Simpson line also points toward the Scottish-Anglo border region as the likely deeper origin of the family.

DNA alone does not prove the identity of William Simson of Kent County. Combined with the documentary record, however, it strongly supports a border-origin Simpson male entering the colonial record in the right period.

The Maryland and Blakiston Connection

The strongest candidate for the elder immigrant is the William Simson named in a Maryland headright claim recorded by John Blakiston. The Blakiston claim credited the transport of several people, including William Simson, in 1668.

This fits the broader historical pattern. Maryland was a more likely entry point for an indentured servant than Delaware. Maryland offered headright incentives and received large numbers of indentured laborers. Delaware, by contrast, did not have the same headright system and was still sparsely settled in this period.

Records also place a William Simson at St. Clement’s Manor in Maryland, where he appears as a resident and was fined by the manor court for allowing hogs to run loose. The timing is consistent with a servant near the end of his indenture or recently free.

The Blakistons later had land and family activity on the Eastern Shore and in the Delaware-connected region. That movement provides a plausible pathway by which Simson could have moved from Maryland servitude into the Kent County, Delaware land transactions.

Alternative William Sim(p)sons

The proof also considers other men named William Simson or Simpson in seventeenth-century records.

These include men appearing in Virginia headright records, a Bristol servant register, New Netherland/New York records, a Maryland headright claimed by Thomas Mountfort, a Talbot County carpenter whose will was proved in 1696, and a Chester County, Pennsylvania landowner.

Each alternative has problems. Some are geographically distant from Kent County, Delaware. Some belong to different social or migration networks. Some have later records that conflict with the 1699 binding-out of a young William Simpson in Delaware. Others appear to have no connection to the local Walker, Edmondson, Brinckloe, Richardson, or Blakiston networks.

The strongest competing possibility is the Mountfort headright entry in Maryland, because Mountfort operated in circles that could have overlapped with John Edmondson. However, that case is weaker than the Blakiston connection because it lacks the same border-region recruitment logic and does not fit the later Kent County evidence as cleanly.

Reconstructed Timeline

  • 1668 or earlier: William Simson likely arrived in Maryland under the headright of John Blakiston, probably as an indentured servant.
  • 1670-1672: He appeared in St. Clement’s Manor records as a resident.
  • 1673-1675: He became involved in the Raccoon Creek land transaction associated with John Edmondson.
  • 1676: William Simson received the 400-acre Kent County, Delaware land grant known as Simpson’s Choice.
  • 1678-1680: The tract passed through John Brinckloe to John Edmondson and then to John Richardson.
  • 1699: A thirteen-and-a-half-year-old William Simpson was bound to John Walker in Kent County. This boy was very likely the son of the earlier William Simson.

Limitations

This conclusion is well supported, but it remains inferential.

No surviving record directly states that the William Simpson bound out in 1699 was the son of William Simson of Simpson’s Choice. No known record explicitly identifies the elder William’s birthplace. No surviving deed has been found in which Simson personally conveys Simpson’s Choice. Early Kent County records are fragmentary, and some deed books survive only in part.

The argument should remain open to revision if new records appear, especially unexamined loose court papers, missing deed fragments, or records that identify another adult William Simson/Simpson in the same region. At present, however, the Blakiston-Simson-Delaware reconstruction best explains the full body of evidence.

Full Proof

For the complete analysis, including citations, maps, alternate William Sim(p)sons, glossary, and appendices, see:

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Sources

court record

1699 William Simpson Binding-Out Record

Citation: Kent County, Delaware, Court Records, p. 10, entry for William Simpson brought into court by John Walker, December 1699; "Kent, Delaware, United States records," images, FamilySearch (https://www.familysearch.org/ark:/61903/3:1:3QHV-F3CK-L9XL-X?view=explore : accessed 23 May 2026), image 139 of 732; court-session context from image 128 of 732; Image Group Number 008664131.

Access: FamilySearch digital image, accessed 23 May 2026.

Supports:
  • A servant boy named William Simpson was in John Walker's custody in December 1699.
  • The court estimated William's age at about thirteen years and six months.
  • The age estimate supports a birth estimate near June 1686 if this boy is the later Mispillion Hundred landholder.